Polyether polymer, preparation process and use thereof

ABSTRACT

The present invention relates to a polyether polymer having structural units represented by general formula (1), wherein R 1  and R 2  mean individually an alkyl group of 1-20 carbon atoms, which may have at least one hydroxyl group, and Y denotes an alkylene group of 1-10 carbon atoms, which may have a hydroxyl group, a preparation process thereof, and a moisturizer, a cosmetic composition and a detergent composition comprising this polymer. The cosmetic composition and detergent composition are excellent in moisture retention, keep up the moisturizing effect over a long period of time and give users a pleasant feeling.

TECHNICAL FIELD

The present invention relates to a novel polyether polymer, andparticularly to a polyether polymer having carbobetaine groups on itsside chains, a preparation process thereof, its use for a moisturizer,and a cosmetic composition and a detergent composition comprising thepolymer.

BACKGROUND ART

Various kinds of moisturizers have heretofore been incorporated in manycosmetic and detergent compositions for the purpose of imparting amoisturized feeling to the user's hair and skin. Low-molecular weightcompounds such as glycerol, propylene glycol, sorbitol, urea and adductsof alkylene oxide with saccharides have been used as such moisturizers.

However, none of these moisturizers have been satisfactory from theviewpoint of moisture retention, a feeling upon use, etc., and involveda problem that they are easily diffused and washed away by sweat and/orwater, and so their effects do not last long. In addition, when they areused in cosmetic compositions which are washed off after their use, suchas rinses and body rinses, or in detergent compositions containing agreat amount of a surfactant, they are almost washed off, and so theirinherent effects cannot be fully exhibited in many cases.

High-molecular weight moisturizers such as collagen, hyaluronic acid andcationized cellulose have also been known. However, these moisturizersare not fully satisfactory from the viewpoint of a feeling upon usebecause they give a sticky feeling to the user's hair and skin or theygive less moisturized feeling.

On the other hand, a moisturizer of the carboxybetaine type is disclosedin EP-A-0649834. However, such a compound has also been diffused andwashed away by sweat and/or water like the moisturizers of thelow-molecular weight compounds, and so the lastingness of itsmoisturizing effect has not been sufficient.

There has thus been a demand for development of a moisturizer which hasexcellent moisture retention, gives users a pleasant feeling and keepsup its moisturizing effect over a long period of time without beingwashed away by sweat and/or water or even after washing off it.

DISCLOSURE OF THE INVENTION

In view of the foregoing circumstances, the present inventors havecarried out an extensive investigation. As a result, it has been foundthat when the side chains, or chloromethyl groups, ofpolyepichlorohydrin are reacted with an amine, and then with aω-halocarboxylic acid (salt) or a cyclic lactone, a polyether polymerhaving carbobetaine groups on its side chains is obtained, and thispolymer not only has excellent moisture retention, but also keeps up itsmoisturizing effect over a long period of time and gives users apleasant feeling when incorporated for use in various cosmetic anddetergent compositions, thus leading to completion of the presentinvention.

It is therefore an object of the present invention to provide a newpolyether polymer and a process for its preparation.

A further object is to provide a new moisturizer having advantageousproperties.

A still further object is to provide a cosmetic composition.

A still further object is to provide a detergent composition.

According to the present invention, there is thus provided a polyetherpolymer having structural units represented by the following generalformula (1): ##STR1## wherein R¹ and R² mean individually an alkyl groupof 1-20 carbon atoms, which may have one or more hydroxyl groups, and Ydenotes an alkylene group of 1-10 carbon atoms, which may have ahydroxyl group.

According to the present invention, there is also provided a process forpreparing a polyether polymer having structural units represented by thegeneral formula (1): ##STR2## wherein R¹ and R² mean individually analkyl group of 1-20 carbon atoms, which may have one or more hydroxylgroups, and Y denotes an alkylene group of 1-10 carbon atoms, which mayhave a hydroxyl group, which comprises reacting a polymer havingstructural units represented by the general formula (2): ##STR3##wherein R¹ and R² have the same meaning as defined above, with aω-halocarboxylic acid or a salt thereof represented by the followinggeneral formula (3) or a cyclic lactone represented by the followinggeneral formula (4): ##STR4## wherein Y has the same meaning as refinedabove, Z denotes a halogen atom, M is a metal ion or a hydrogen atom,and m stands for a number of 1-8.

According to the present invention, there is further provided amoisturizer comprising, as an active ingredient, the polyether polymerhaving the structural units represented by the general formula (1).

According to the present invention, there is still further provided useof the polyether polymer having the structural units represented by thegeneral formula (1) for a moisturizer.

According to the present invention, there is yet still further provideda cosmetic composition comprising the polyether polymer having thestructural units represented by the general formula (1).

According to the present invention, there is yet still further provideda detergent composition comprising the polyether polymer having thestructural units represented by the general formula (1), and detergentingredients.

BEST MODE FOR CARRYING OUT THE INVENTION

The polyether polymer according to the present invention is requiredonly to have the structural units represented by the general formula (1)in its molecule and may be either a polymer composed simply of suchstructural units or a copolymer with those having other side chains inthis structural unit, or with one or more kinds of other structuralunits. In the case of the copolymer, those having different side chainsin the structural unit represented by the general formula (1) may bebonded to each other in the form of either a block copolymer or a randomcopolymer, or it does not also care about the bonding configuration ofthe principal chain in the copolymer, i.e., whether the principal chainis formed by head-to-tail linkage or by head-to-head linkage.

In the general formula (1), R¹ and R² mean individually an alkyl groupof 1-20 carbon atoms, which may have at least one hydroxyl group.Specific examples thereof include methyl, ethyl, propyl, butyl, pentyl,hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl,tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl,eicosyl, 2-hydroxyethyl, 3-hydroxypropyl, 4-hydroxybutyl,5-hydroxypentyl, 6-hydroxyhexyl, 7-hydroxyheptyl, 8-hydroxyoctyl,9-hydroxynonyl, 10-hydroxydecyl, 11-hydroxyundecyl, 12-hydroxydodecyl,13-hydroxytridecyl, 14-hydroxytetradecyl, 15-hydroxypentadecyl,16-hydroxyhexadecyl, 17-hydroxyheptadecyl, 18-hydroxyoctadecyl,19-hydroxynonadecyl, 20-hydroxyeicosyl, 2,3-dihydroxypropyl and2,3,4,5-tetrahydroxypentyl groups, and the like. Of these, alkyl groupsof 1-5 carbon atoms, which may have at least one hydroxyl group, arepreferred, with 2-hydroxyethyl, 3-hydroxypropyl, 4-hydroxybutyl,5-hydroxypentyl, 2,3-dihydroxypropyl, methyl, ethyl, propyl, butyl andpentyl being particularly preferred. R¹ and R² may be identical with ordifferent from each other. In particular, it is preferred that R¹ be analkyl group having 1-5 carbon atom, while R² be a ω-hydroxyalkyl grouphaving 1-5 carbon atoms.

Examples of the alkylene group of 1-10 carbon atoms, which is indicatedby Y and may have a hydroxyl group, include methylene, ethylene,propylene, trimethylene, tetramethylene, pentamethylene, hexamethylene,heptamethylene, octamethylene, nonamethylene, decamethylene,hydroxymethylene, hydroxyethylene and hydroxymethylmethylene groups, andthe like. Of these, those having 1-5 carbon atoms are preferred, withmethylene and ethylene groups being particularly preferred.

Specific examples of the structural unit represented by the generalformula (1) include those represented by the following formulae (a) to(d): ##STR5## wherein A and D mean, independently of each other, ahydrogen atom or a hydroxyl group, u and v are, independently of eachother, a number of 1-20, and w is a number of 1-10.

In the above formulae, it is preferred that u and v be, independently ofeach other, a number of 1-5 when A and/or D is OH. It is also preferredthat w be a number of 1-5.

Of these, a structural unit represented by the following formula (a-1),(a-2), (a-3) or (d-1) is more preferred. ##STR6##

The polyether polymer according to the present invention may be acopolymer composed of the structural unit represented by the generalformula (1) hereinafter referred to as the structural unit (1)! and oneor more structural units other than this structural unit. The otherstructural units may preferably be etheric structural units. Examplesthereof include those represented by the following formulae (e) to (i)hereinafter referred to as the structural units (e) to (i),respectively!. ##STR7##

In the formula (e), R³ means --H, --CH₃, --CH₂ OH, --CH₂ --O--CH₂ CH(OH)--CH₂ OH, --CH₂ OR⁸, --CH₂ SR⁸ or --CH₂ S(CH₂)₃ SR⁸ in which R⁸ is analkyl, alkenyl, cycloalkyl, aralkyl or aryl group having 1-20 carbonatoms.

In the formula (g), R⁴ denotes a cationic group represented by thefollowing formula (g-1), (g-2) or (g-3): ##STR8## wherein b and c areindividually a number of 1-10, d is a number of 0-2, e is a number of0-3, f is a number of 1-20, and X⁻ denotes a counter anion.

In the formula (h), R⁵ means --SO₃ M or --O--CH₂ --COOM in which M is ametal ion such as sodium or potassium, or a hydrogen atom.

In the formula (i), R⁶ and R⁷ mean individually an alkyl group of 1-20carbon atoms, which may have one or more hydroxyl groups, and a is anumber of 1-10.

As the counter anion X⁻, a halogen ion such as a chlorine or bromineion, a methylsulfate ion or an ethyl-sulfate ion is preferred.

Of these structural units, the structural units (e), (g) and (h) aremore preferred. With respect to the structural unit (e), those, in whichR³ is --H, --CH₂ OH or --CH₂ --O--R^(8') (R^(8') : an alkyl or arylgroup having 6-18 carbon atoms), are preferred. With respect to thestructural unit (g), those, in which R⁴ is a group represented by anyone of the following formulae: ##STR9## are preferred. With respect tothe structural unit (h), those, in which M is a sodium atom, arepreferred.

In a polymer or a copolymer of the structural unit (1), which maycontain one or more of the structural units (e) to (i), it is preferredthat the structural unit (1) be contained in a proportion of 10-100 wt.%, particularly 50-100 wt. % based on the total weight of the copolymer.It is also preferred that the structural units (e) and (f) be containedin proportions of 0-90 wt. %, and the structural units (g), (h) and (i)be contained in proportions of 0-50 wt. %.

These other structural units can be introduced by a process in whichtheir corresponding oxirane compounds are copolymerized withepichlorohydrin, a process in which an epichlorohydrin (co)polymer issubjected to a functional group conversion reaction in accordance withthe conventional method, or the like.

Among such copolymers, copolymers composed of the structural unit (1)and the structural unit (e), (g), (h) or (i) are preferred, withcopolymers composed of the structural unit (1) and the structural unit(e) and/or (g) being particularly preferred.

The polyether polymer according to the present invention preferably hasa weight-average molecular weight of 500-1,000,000, more preferably1,000-500,000, most preferably 5,000-100,000. Any (co)polymer having aweight-average molecular weight within this range is preferred becauseit has high moisturizing ability and gives users a pleasant feeling.

The polyether polymer according to the present invention can be preparedby reacting a polymer (aminated polyepichlorohydrin) having structuralunits represented by the general formula (2) with a ω-halocarboxylicacid or a salt thereof (3), or a cyclic lactone (4) in accordance with,for example, the following reaction scheme: ##STR10## wherein m standsfor a number of 1-8, and R¹, R², Y, Z and M have the same meaning asdefined above.

The aminated polyepichlorohydrin (2) as used herein can be obtained byusing polyepichlorohydrin or its copolymer with one or more otherstructural units, and a secondary amine to conduct an amination reactionin accordance with, for example, the process described in DE U.S. Pat.No. 2,540,310. A (co)polymer corresponding to the aminatedpolyepichlorohydrin (2) can be synthesized by reactingpolyepichlorohydrin or its copolymer with one or more other structuralunits and a primary amine, and then reacting the resultant product withethylene oxide.

The polyepichlorohydrin can be synthesized in accordance with, forexample, the process described in Journal of Polymer Science, PolymerChemistry Edition, Vol. 13, 1993 (1975). For example, epichlorohydrin ispolymerized at room temperature to 40° C. in the presence of apolymerization catalyst composed of triethylaluminum and water inchlorobenzene as a solvent, whereby polyepichlorohydrin can be obtained.Besides, the copolymer with the other structural units can be obtainedby copolymerizing epichlorohydrin with, for example, a monomer such asethylene oxide or allyl glycidyl ether in an autoclave. As thepolyepichlorohydrin or the copolymer of epichlorohydrin and anothermonomer, there may be used commercially-available products such asGechron® 1000, Gechronr® 2000 and Gechron® 3102 (products of Nippon ZeonCo., Ltd.); Epichlomer® H, Epichlomer® C and Epichlomer® CG (products ofDaiso Co., Ltd.); and Herclor® H and Herclor® C (products of HerculesInc.). These polymers such as polyepichlorohydrin preferably have aweight-average molecular weight of 2,000-1,500,000 from the viewpoint ofhandling and achievement of good properties.

The secondary amine used in the amination reaction may have at least oneprimary or secondary hydroxyl group. Examples thereof includedimethylamine, diethylamine, methylethylamine, methyethanolamine,diethanolamine and secondary amines synthesized by reacting an oxiranecompound such as epichlorohydrin or glycidol with a primary amine suchas methylamine. These secondary amines are preferably used in an amountof generally 1-10 equivalents to the chlorine content in thepolyepichlorohydrin. As the primary amine, there may be usedmethylamine, ethylamine, propylamine or the like. The primary amine ispreferably used in an amount of 1-10 equivalents to the chlorine contentin the polyepichlorohydrin. In order to sebsequently add ethylene oxideto the reaction product of the primary amine, ethylene oxide may be usedin an amount of 1-10 equivalents per equivalent of the amine.

Examples of a reaction solvent used in the amination reaction includeprotonic or aprotic polar solvents such as acetonitrile, water,methanol, ethanol, chloroform, tetrahydrofuran, dimethylformamide,dimethyl sulfoxide and N-methylpyrrolidone, and nonpolar solvents suchas toluene and xylene. Dimethylformamide, dimethyl sulfoxide,N-methylpyrrolidone and the like, which are polar aprotic solvents, aswell as toluene and xylene, which are nonpolar solvents, are morepreferred.

The reaction may preferably be conducted at 80°-150° C., particularly90°-130° C. It is also preferable to conduct the reaction under pressurein an autoclave depending on the reaction conditions such as the use ofan amine having a boiling point lower than ordinary temperature.

The aminated polyepichlorohydrin (2) thus obtained is reacted with aω-halocarboxylic acid or a salt thereof (3), or a cyclic lactone (4) toform a betaine compound. Examples of the ω-halocarboxylic acid or thesalt thereof (3) used herein include chloroacetic acid, sodiumchloroacetate, potassium chloroacetate, 3-bromopropionic acid, sodium3-bromopropionate, potassium 3-bromopropionate, 6-bromohexanoic acid,sodium 6-bromohexanoate, potassium 6-bromohexanoate, 11-bromoundecanoicacid, sodium 11-bromoundecanoate and potassium 11-bromoundecanoate.These compounds are preferably used in an amount of generally 1-5equivalents, particularly 1-2 equivalents to the aminatedpolyepichlorohydrin (2).

Examples of the cyclic lactone (4) include β-propiolactone,γbutyrolactone, δ-valerolactone and ε-caprolactone. These cycliclactones are preferably used in an amount of 0.95-2 equivalents,particularly 0.98-1.02 equivalents to the aminated polyepichlorohydrin(2).

As the ω-halocarboxylic acid or the salt thereof (3), or the cycliclactone (4), which is to be reacted with the aminatedpolyepichlorohydrin (2), ω-halocarboxylic acids having 2-7 carbon atoms,β-propiolactone and γ-butyrolactone are preferred.

In the reaction for forming the betaine compound, a polar protic solventis used as a reaction solvent. Preferable examples thereof includewater, alcohols (methanol, ethanol, 2-propanol, etc.), and mixedsolvents composed of water and an alcohol.

The reaction is preferably conducted at 40°-100° C., particularly60°-85° C.

After the amination reaction and/or the reaction of the formation of thebetaine compound, the resulting polymer may also be treated with theconventional decoloring agent, for example, borohydride compounds suchas sodium borohydride to improve the hue of the polymer.

Among the polyether polymers according to the present invention, thecopolymers composed of the structural unit (1) and the other structuralunit(s) can be prepared by using, as a starting material, a copolymercomposed of epichlorohydrin and the,other structural unit(s) in asimilar manner to that described above.

For example, a copolymer, which contains, as structural units, those inwhich R⁴ in the structural unit (g) is represented by the formula (g-2),can be obtained by using, for example, polyepichlorohydrin as a startingmaterial polymer to aminate the polymer in the same manner as describedabove, quaternizing side chains, or aminated functional groups, of theaminated polymer with a quaternizing agent such as an alkyl halide atthe desired compositional ratio and then reacting the thus-quaternizedproduct with a ω-halocarboxylic acid or a salt thereof, or a cycliclactone.

Since the thus-obtained polyether polymers (1) according to the presentinvention have a function which combines moisture retention (waterretention) with adsorptivity on the hair and skin, and also possess goodhydrophilicity, they are useful as moisturizers.

Accordingly, a moisturizer according to the present invention, whichcomprises, as an active ingredient, the polyether polymer (1), givesusers an excellent moisturized feeling and keeps up its effect over along period of time when applied to the hair and/or skin, and can hencebe used in various applications, e.g., cosmetic and detergentcompositions.

One or more of the polyether polymers are incorporated into the cosmeticcompositions according to the present invention. The polyether polymersare preferably incorporated in a proportion of 0.001-20 wt. %(hereinafter indicated merely by "%") based on the total weight of thecomposition. In particular, it is preferred that they be incorporated ina proportion of 0.05-10%, most preferably 0.1-5% because a propermoisturized feeling lasts for a long period of time.

In the cosmetic compositions according to the present invention, asneeded, those routinely employed as cosmetic ingredients, for example,higher alcohols having a straight-chain or branched alkyl or alkenylgroup; hydrocarbons such as liquid paraffin, vaseline and solidparaffin; lanolin derivatives such as liquid lanolin and lanolin fattyacid; phospholipids such as lecithin; sterols such as cholesterol, andderivatives thereof; collagenolytic peptide derivatives;fluorine-containing oily bases such as perfluoropolyether; oils and fatssuch as esters of higher alcohols with higher fatty acids, higher fattyacids and long-chain amidoamines having an alkyl or alkenyl group;animal and vegetable oils and fats such as mink oil and olive oil;nonionic surfactants, anionic surfactants, amphoteric surfactants andcationic surfactants; antidandruff agents such as zinc pyrithione andOctopirox (piroctone ethanolamine salt); disinfectants such as triclosanand triclocarban; antiinflammatory agents such as dipotassiumglycyrrhetinate and tocopheryl acetate; medicinally-effectiveingredients such as blood circulation-facilitating agents, skinactivators and vitamins; antiseptics such as parabens; viscositymodifiers such as methylcellulose, ethylcellulose, hydroxycellulose,carboxyvinyl polymers, xanthan gum, guar gum and ethanol; colorants suchas dyes and pigments; ultraviolet absorbents; other moisturizers such aspropylene glycol, glycerol, carbitol, 3-methyl-1,3-butanediol andsaccharides; astringents; perfume bases; coloring matters; etc., may besuitably incorporated in addition to the essential ingredient describedabove within limits not impeding the effects of the present invention.

The cosmetic compositions according to the present invention may beprepared in accordance with a method known per se in the art and may beformulated in any forms such as liquid, cream, solid and powder.However, it is particularly preferred that they be formulated in theform of liquid or cream.

One or more of the polyether polymers are incorporated into thedetergent compositions according to the present invention. The polyetherpolymers are preferably incorporated in a proportion of 0.05-20% basedon the total weight of the composition. In particular, it is preferredthat they be incorporated in a proportion of 0.1-10%, most preferably0.2-5% because a proper moisturized feeling lasts for a long period oftime even after the composition is used in washing and washed off.

In the detergent compositions according to the present invention,detergent ingredients, usually, various kinds of surfactants employed indetergent compositions, may be optionally used within limits notimpeding the effects of the present invention.

More specifically, examples of anionic surfactants to be used includesulfate and sulfonate type surfactants such as alkylsulfates,polyoxyethylene alkylsulfates, sulfosuccinates, taurates, isethionatesand α-olefin-sulfonates; carboxylate type surfactants such as fatty acidsoaps, ether carboxylate surfactants and acylated amino acidsurfactants; and phosphate type surfactants such as alkyl-phosphates. Ofthese, the surfactants of the fatty acid soap, sulfate and isethionatetypes are particularly preferred from the viewpoint of a feeling uponuse and foaming.

Examples of amphoteric surfactants include carbobetaine, sulfobetaineand imidazolium betaine type amphoteric surfactants.Hydroxypropylsulfobetaine, desalted secondary imidazolinium betaine andthe like are preferably used.

Examples of nonionic surfactants include surfactants of thepolyoxyalkylene-added type, polyoxypropylene- and polyoxyethylene-addedtype, amine oxide type, mono- or diethanolamide type, and polyhydricalcohol type such as sorbitan fatty acid esters, glycerol fatty acidesters sucrose fatty acid esters, alkylsaccharides andN-polyhydroxyalkyl fatty acid amides. In particular, nonionicsurfactants of the amine oxide, diethanolamide and alkylsaccharide typesare preferably used.

Examples of cationic surfactants include mono- or dialkyl-addedquaternary ammonium salts having a straight-chain or branched alkylgroup and alkylene oxide adducts thereof, said alkylene oxide beingadded to the alkyl group(s) of the ammonium salts. In particular,quaternary ammonium salts having a straight-chain monoalkyl group of12-16 carbon atoms or a branched alkyl group of 20-28 carbon atoms arepreferably used.

These surfactants may be used either singly or in any combinationthereof and are preferably incorporated in a proportion of 2-60%,particularly 5-50% based on the total weight of the detergentcomposition.

Besides, these surfactants are preferably used in a proportion rangingfrom 5 to 10,000 parts by weight, particularly from 10 to 1,000 parts byweight per part by weight of the polyether polymer.

In the detergent compositions according to the present invention, otheringredients routinely employed in detergent compositions, for example,polyhydric alcohols such as ethylene glycol, polyethylene glycols,propylene glycol, polypropylene glycols, butylene glycols, glycerol,polyglycerols, sugar alcohols, etc.; oily ingredients, such ashydrocarbons such as liquid paraffin, squarane, vaseline and solidparaffin, natural oils such as olive oil, jojoba oil, evening primroseoil, coconut oil and beef tallow, ester oils such as isopropylmyristate, cetyl isooctanoate and neopentylglycol dicaprate, siliconeoils such as dimethylsilicone and methylphenylsilicone, and higher fattyacids such as isostearic acid and oleic acid; medicinally-effectiveingredients such as vitamins, disinfectants, antiinflammatory agents,antidandruff agents, activators, cold sensation-imparting agents andultraviolet absorbents; water-swelling clay minerals such asmontmorillonite, saponite, hectorite, beagum, cunivia and smectone;polymers, such as polysaccharides such as karrageenan, xanthan gum,sodium alginate, pullulan, methylcellulose, carboxymethyl-cellulose,hydroxyethylcellulose and hydroxypropylcellulose, and synthetic polymerssuch as carboxyvinyl polymers and polyvinyl pyrrolidone; pigments, suchas inorganic pigments such as titanium oxide, kaolin, mica, sericite,zinc white and talc, and polymeric powders such as poly(methylmethacrylate) powder and nylon powder; antiseptics such as methylparabenand butylparaben; viscosity modifiers such as inorganic salts,polyethylene glycol stearate and ethanol; pearly luster-impartingagents; perfume bases; coloring matters; antioxidants; and the like, maybe suitably incorporated in addition to the above ingredients withinlimits not impeding the effects of the present invention.

The detergent compositions according to the present invention may beprepared in accordance with a method known per se in the art and may beformulated in any forms such as liquid, paste, solid and powder.However, it is particularly preferred that they be formulated in theform of liquid or paste. The detergent compositions according to thepresent invention are preferably provided as detergents which have apossibility that they may come contact with the skin and/or the hair,such as skin detergents, hair detergents and diswashing detergents.

As described above, the polyether polymers according to the presentinvention have high water retention, adsorbability and hydrophilicity,and are hence useful not only for cosmetic composition and detergentcompositions, but also for various chemicals, for example, flocculants,antistatic agents, surface modifiers, dispersants, anti-fogging agents,soiling preventives, etc., which are applied on the surface of variousmaterials such as metals, glasses, ceramics and plastics.

EXAMPLES

The present invention will hereinafter be described more specifically bythe following examples. However, the present invention is not intendedto be limited to these examples.

Preparation Example 1

In an autoclave purged with nitrogen, 15 g of polyepichlorohydrin("Gechron® 1000", product of Nippon Zeon Co., Ltd.) were dissolved in135 g of N-methylpyrrolidone while stirring at 80° C. The solution wasthen chilled with ice water. A 50% aqueous solution of dimethylamine inan amount of 146 g was heated to 80° C., and dimethylamine gas generatedwas introduced into the autoclave to dissolve in the reaction solutionwhile bubbling until the dimethylamine gas ceased to be generated. Afterthe system was hermetically sealed to conduct a reaction at 120° C. for12 hours, the system was opened to remove effluent gas. The reactionsolution was cooled to room temperature and then subjected toreprecipitation in isopropyl ether in an amount 10 times of the reactionsolution. The resultant precipitate was dissolved in ion-exchangedwater, and the aqueous solution was subjected to a desalting treatmentwith a strongly basic ion-exchange resin ("IRA-402", product of JapanOrgano Co., Ltd.) and then lyophilized, thereby obtaining an aminatedpolymer.

In a reaction vessel equipped with a reflux condenser, 23.34 g of sodiummonochloroacetate were then suspended in 150 g of methanol. After 13.51g of the aminated polymer were added to the suspension with stirring, areaction was conducted for 24 hours under reflux of methanol. Thereaction solution was cooled, and deposited insoluble matter wascollected by filtration and then subjected to reprecipitation in a mixedsolvent of ethanol/acetone (1/5 v/v) in an amount 10 times of thereaction solution. The resultant precipitate was dissolved inion-exchanged water, and the aqueous solution was treated with acation/anion mixed type ion-exchange resin ("IRA-120B"/"IRA-402",product of Japan Organo Co., Ltd.). The thus-treated aqueous solutionwas lyophilized to obtain 17.53 g of a polyether polymer. An NMRanalysis revealed that this polymer is apolyoxyethylene-dimethylaminocarbobetaine polymer having the followingstructural units: ##STR11##

NMR (D₂ O, 200 MHz, ppm): 3.27(6H,s, --N(CH₃)₂), 3.5-4.34(7H,m, --CH₂--CH--O--, --CH₂ --N⁺ --CH₂ --COO⁻).

Molecular weight (GPC, 0.2M phosphate buffer, PEG standard): Mw=7,000;Mn=2,000.

Preparation Example 2

In a 0.5-liter reaction vessel, 15 g of polyepichlorohydrin rubber("Gechron® 1000", product of Nippon Zeon Co., Ltd.) were dissolved in135 g of N-methylpyrrolidone while stirring at 80° C. in a nitrogenstream. After 60.84 g of N-methylethanolamine were added to thesolution, a reaction was conducted at 120° C. for 6 hours. The reactionsolution was distilled at 110° C. under reduced pressure (5 mmHg) toremove a distillate, thereby obtaining a viscous substance. Theresultant viscous substance was dissolved in ion-exchanged water, andthe aqueous solution was subjected to a desalting treatment with astrongly basic ion-exchange resin ("IRA-402", product of Japan OrganoCo., Ltd.) and then lyophilized, thereby obtaining an aminated polymer.

In a reaction vessel equipped with a reflux condenser, 28.3 g of sodiummonochloroacetate were then suspended in 200 g of ethanol. After 21.3 gof the aminated polymer were added to the suspension, ion-exchangedwater was added until the suspended sodium monochloroacetate wasdissolved. After a reaction was conducted for 36 hours under reflux, thereaction solution was subjected to reprecipitation in a mixed solvent ofacetone/methanol (2/1 v/v) in an amount 20 times of the reactionsolution. The resultant precipitate was dissolved in ion-exchangedwater, and the aqueous solution was subjected to a desalting treatmentwith a cation/anion mixed type ion-exchange resin ("IRA-120B"/"IRA-402",product of Japan Organo Co., Ltd.). The thus-desalted aqueous solutionwas lyophilized to obtain 21.9 g of a polyether polymer. An NMR analysisrevealed that this polymer is apolyoxyethylene-methylhydroxyethylamino-carbobetaine polymer having thefollowing structural units: ##STR12##

NMR (D₂ O, 200 MHz, ppm): 2.95(3H,s, --N--CH₃), 3.10-3.55(7H,m, --CH₂--CH--O--, --CH₂ --N⁺ --CH₂ --CH₂ --OH), 3.55-4.00(4H,m, --CH₂ --OH,--N⁺ --CH₂ --COO⁻).

Molecular weight (GPC, 0.2M phosphate buffer, PEG standard): Mw=15,000;Mn=6,700.

Preparation Example 3

In an autoclave purged with nitrogen, 15 g of polyepichlorohydrin("Gechron® 1000", product of Nippon Zeon Co., Ltd.) were dissolved in135 g of N-methylpyrrolidone while stirring at 80° C. The solution wasthen chilled with ice water. A 50% aqueous solution of dimethylamine inan amount of 146 g was heated to 80° C., and dimethylamine gas generatedwas introduced into the autoclave to dissolve in the reaction solutionwhile bubbling until the dimethylamine gas ceased to be generated. Afterthe system was hermetically sealed to conduct a reaction at 120° C. for12 hours, the system was opened to remove effluent gas. The reactionsolution was cooled to room temperature and then subjected toreprecipitation in isopropyl ether in an amount 10 times of the reactionsolution. The resultant precipitate was dissolved in ion-exchangedwater, and the aqueous solution was subjected to a desalting treatmentwith a strongly basic ion-exchange resin ("IRA-402", product of JapanOrgano Co., Ltd.) and then lyophilized, thereby obtaining an aminatedpolymer.

In a reaction vessel equipped with a reflux condenser, 13.5 g of theaminated polymer and 2.1 g of lauryl chloride were dissolved in 150 g ofmethanol to conduct a reaction for 12 hours under reflux. Then, 16.2 gof sodium monochloroacetate were added to the solution, followed by areaction for 36 hours under reflux. The reaction solution was cooled,and deposited insoluble matter was collected by filtration and thensubjected to reprecipitation in acetone in an amount 10 times of theinsoluble matter. The resultant precipitate was dissolved inion-exchanged water, and the aqueous solution was subjected to adesalting treatment with a cation/anion mixed type ion-exchange resin("G-10", product of Japan Organo Co., Ltd.). The aqueous solution wastitrated and neutralized to pH 7 using a pH meter, and then lyophilized,thereby obtaining 21.5 g of a polyether polymer. An NMR analysisrevealed that this polymer is a polymer (a molar ratio, p/q betweenindividual structural units p and q: 92.5/7.5) having the followingstructural units: ##STR13##

NMR (D₂ O, 200 MHz, ppm): 0.78(3H,t,CH₃ --(CH₂)₁₁ --), 1.19(20H,m,CH₃--(CH₂)₁₀ --CH₂ --), 3.78(8H,m, --N(CH₃)₂, CH₃ --(CH₂)₁₀ --CH₂ --),3.46-4.15(9H,m, --CH₂ --CH--O--, --CH₂ --N⁺ --CH₂ --COO⁻), 4.15(2H,brs,--N⁺ --CH₂ --COO⁻).

Molecular weight (GPC, 0.2M phosphate buffer, PEG standard): Mw=9,400;Mn=4,700.

Preparation Example 4

In a 0.5-liter reaction vessel, 15 g of polyepichlorohydrin rubber("Gechron® 1000", product of Nippon Zeon Co., Ltd.) were dissolved in135 g of N-methylpyrrolidone while stirring at 80° C. in a nitrogenstream. After 85.2 g of diethanolamine were added to the solution, areaction was conducted at 125° C. for 6 hours. The reaction solution wascooled to room temperature and then subjected to reprecipitation inacetone in an amount 20 times of the reaction solution. Thethus-obtained viscous substance was dissolved again in methanol, and themethanol solution was subjected to reprecipitation in ethyl acetate inan amount 10 times of the methanol solution. The resultant precipitatewas dissolved in ion-exchanged water, and the aqueous solution wassubjected to a desalting treatment with a strongly basic ion-exchangeresin ("IRA-402", product of Japan Organo Co., Ltd.) and thenlyophilized, thereby obtaining an aminated polymer.

In a reaction vessel equipped with a reflux condenser, 12.1 g of sodiummonochloroacetate were then added to 120 ml of a mixed solvent ofethanol and water (2/1 v/v). After 11.2 g of the aminated polymer wereadded to the mixture, a reaction was conducted for 36 hours underreflux. The reaction solution was concentrated by means of anevaporator, and the concentrate was subjected to a desalting treatmentwith a cation/anion mixed type ion-exchange resin ("IRA-120B"/"IRA-402",product of Japan Organo Co., Ltd.). The thus-desalted aqueous solutionwas lyophilized. The thus-obtained polymer was dissolved in 200 ml ofmethanol, and the solution was subjected to reprecipitation in acetonein an amount 10 times of the solution. The resultant precipitate waslyophilized to obtain 8.6 g of a polyether polymer. An NMR analysisrevealed that this polymer is a polymer having the following structuralunits: ##STR14##

NMR (D₂ O, 200 MHz, ppm): 3.15-4.15(15H,m, all protons). Molecularweight (GPC, 0.2M phosphate buffer, PEG standard): Mw=71,000; Mn=46,000.

Preparation Example 5

In a 0.5-liter reaction vessel, 40 g of glycidol were added dropwise to210 g of a 40% aqueous solution of methylamine cooled with water over 2hours, followed by the reaction of the reaction solution at 50° C for 5hours in a nitrogen stream. The reaction solution was distilled at 70°C. under reduced pressure (5 mmHg) to remove a distillate, therebyobtained a secondary amine (glyceromonomethylamine). In a nitrogenstream, 15 g of polyepichlorohydrin ("Gechron® 1000", product of NipponZeon Co., Ltd.) were dissolved in 135 g of N-methylpyrrolidone whilestirring at 80° C. After glyceromonomethylamine was added to thesolution, a reaction was conducted at 125° C. for 24 hours. The reactionsolution was then subjected to reprecipitation in hot acetone in anamount 20 times of the reaction solution, thereby obtaining a viscoussubstance. The viscous substance was dissolved in ion-exchanged water,and the aqueous solution was subjected to a desalting treatment with astrongly basic ion-exchange resin ("IRA-402", product of Japan OrganoCo., Ltd.) and then lyophilized, thereby obtaining an aminated polymer.

In a reaction vessel, 20.6 g of sodium monochloroacetate were then addedto 150 ml of a mixed solvent of ethanol and water (2/1 v/v). After 19 gof the aminated polymer were added to the mixture, a reaction wasconducted for 36 hours under reflux. The reaction solution was subjectedto reprecipitation in a mixed solvent of methanol/2-propanol (1/3 v/v)in an amount 10 times of the reaction solution. The resultantprecipitate was dissolved in ion-exchanged water, and the aqueoussolution was subjected to a desalting treatment with a cation/anionmixed type ion-exchange resin ("IRA-120B"/"IRA-402", product of JapanOrgano Co., Ltd.). The thus-desalted aqueous solution was lyophilized toobtain 13 g of a polyether polymer. An NMR analysis revealed that thispolymer is a polymer having the following structural units: ##STR15##

NMR (D₂ O, 200 MHz, ppm): 3.1(3H,brs, --N--CH₃), 3.4-4.1(12H,m, --CH₂--CH--O--,--CH₂ --N⁺ --CH₂ --COO⁻, --CH₂ --CH(OH)--CH₂ --OH).

Molecular weight (GPC, 0.2M phosphate buffer, PEG standard): Mw=64,000;Mn=17,000.

Preparation Example 6

In an autoclave purged with nitrogen, 15 g of apoly(epichlorohydrin-glycidol) copolymer synthesized by controlling thefunctional group conversion rate of a polyepichlorohydrin in accordancewith Journal of Polymer Science, Polymer Chemistry Edition, Vol. 13,1993 (1975) were dissolved in 135 g of N-methylpyrrolidone whilestirring at 80° C. The system was then chilled with ice water. A 50%aqueous solution of dimethylamine in an amount of 76 g was heated to 80°C., and dimethylamine gas generated was introduced into the autoclave todissolve in the reaction solution while bubbling until the dimethylaminegas ceased to be generated. After the system was hermetically sealed toconduct a reaction at 120° C. for 12 hours, the system was opened toremove effluent gas. The reaction solution was cooled to roomtemperature and then subjected to reprecipitation in isopropyl ether inan amount 10 times of the reaction solution. The resultant precipitatewas dissolved in ion-exchanged water, and the aqueous solution wassubjected to a desalting treatment with a strongly basic ion-exchangeresin ("IRA-402", product of Japan Organo Co., Ltd.) and thenlyophilized, thereby obtaining an aminated polymer.

In a reaction vessel equipped with a reflux condenser, 8.53 g of sodiummonochloroacetate were then suspended in 150 g of methanol. After 15 gof the aminated polymer were added to the suspension, a reaction wasconducted for 24 hours under reflux of methanol. The reaction solutionwas cooled, and deposited insoluble matter was collected by filtrationand then subjected to reprecipitation in acetone in an amount 10 timesof the insoluble matter. The resultant precipitate was dissolved inion-exchanged water, and the aqueous solution was subjected to adesalting treatment with a cation/anion mixed type ion-exchange resin("IRA-120B"/"IRA-402", product of Japan Organo Co., Ltd.). The desaltedaqueous solution was lyophilized to obtain 10 g of a polyether polymer.An NMR analysis revealed that this polymer is a polymer (a molar ratio,p/q between individual structural units p and q: 90/10) having thefollowing structural units: ##STR16##

NMR (D₂ O, 200 MHz, ppm): 3.27(6H,s, --N(CH₃)₂), 3.5-4.34(12H,m, --CH₂--CH--O--, --CH₂ --N⁺ --CH₂ --COO⁻, --CH₂ --OH).

Molecular weight (GPC, 0.2M phosphate buffer, PEG standard):

Mw=5,500; Mn=3,400.

Preparation Example 7

In an autoclave purged with nitrogen, 15 g of apoly(epichlorohydrin-ethylene oxide-glyceryl glycidyl ether) copolymerobtained by treating a poly(epichlorohydrin-ethylene oxide-allylglycidyl ether) copolymer ("Gechron® 3102", product of Nippon Zeon Co.,Ltd.) with m-chloroperbenzoic acid/alkali were dissolved in 135 g ofN-methylpyrrolidone while stirring at 80° C. The system was then chilledwith ice water. A 50% aqueous solution of dimethylamine in an amount of80.8 g was heated to 80° C., and dimethylamine gas generated wasintroduced into the autoclave to dissolve in the reaction solution whilebubbling until the dimethylamine gas ceased to be generated. After thesystem was hermetically sealed to conduct a reaction at 120° C. for 12hours, the system was opened to remove effluent gas. The reactionsolution was cooled to room temperature and then subjected toreprecipitation in isopropyl ether in an amount 10 times of the reactionsolution. The resultant precipitate was dissolved in ion-exchangedwater, and the aqueous solution was subjected to a desalting treatmentwith a strongly basic ion-exchange resin ("IRA-402", product of JapanOrgano Co., Ltd.) and then lyophilized, thereby obtaining an aminatedpolymer.

In a reaction vessel equipped with a reflux condenser, 8.53 g of sodiummonochloroacetate were then suspended in 150 g of methanol. After 15 gof the aminated polymer were added to the suspension, a reaction wasconducted for 24 hours under reflux of methanol. The reaction solutionwas cooled, and deposited insoluble matter was collected by filtrationand then subjected to reprecipitation in acetone in an amount 10 timesof the insoluble matter. The resultant precipitate was dissolved inion-exchanged water, and the aqueous solution was subjected to adesalting treatment with a cation/anion mixed type ion-exchange resin("IRA-120B"/"IPA-402", product of Japan Organo Co., Ltd.). The desaltedaqueous solution was lyophilized to obtain 8 g of a polyether polymer.An NMR analysis revealed that this polymer is a polymer (a molar ratio,p/q/r among individual structural units p, q and r: 47/48/5) having thefollowing structural units: ##STR17##

NMR (D₂ O, 200 MHz, ppm): 3.27(6H,s, --N(CH₃)₂), 3.3-4.34(21H,m, --CH₂--CH--O--, --CH₂ --N⁺ --CH₂ --COO⁻, --CH₂ --O--CH₂ --CH(OH) --CH₂ --OH).

Molecular weight (GPC, 0.2M phosphate buffer, PEG standard): Mw=624,000;Mn=24,000.

Preparation Example 8

In a 0.5-liter reaction vessel, 15 g of polyepichlorohydrin rubber("Gechron® 1000", product of Nippon Zeon Co., Ltd.) were dissolved in135 g of N-methylpyrrolidone while stirring at 80° C. in a nitrogenstream. After 20.6 g of N-methylethanolamine were added to the solution,a reaction was conducted at 120° C. for 6 hours. The reaction solutionwas subjected to reprecipitation in a mixed solvent of ethylacetate/hexane (1/1 v/v), thereby obtaining a viscous substance. Theresultant viscous substance was dissolved in ion-exchanged water, andthe aqueous solution was subjected to a desalting treatment with astrongly basic ion-exchange resin ("IRA-402", product of Japan OrganoCo., Ltd.) and then concentrated under reduced pressure by means of anevaporator. The concentrate was then dissolved in methanol, and themethanol solution was subjected again to reprecipitation in a mixedsolvent of ethyl acetate/hexane (1/1 v/v), thereby obtaining 19 g of anaminated polymer.

In a reaction vessel equipped with a reflux condenser, 15.35 g of sodiummonochloroacetate were then suspended in 200 g of ethanol. After 19 g ofthe aminated polymer were added to the suspension with stirring,ion-exchanged water was added until the suspended sodiummonochloroacetate was dissolved. After a reaction was conducted for 36hours under reflux, the reaction solution was subjected toreprecipitation in a mixed solvent of acetone/ethanol (2/1 v/v) in anamount 10 times of the reaction solution. The resultant precipitate wasdissolved in ion-exchanged water, and the aqueous solution was subjectedto a desalting treatment with a cation/anion mixed type ion-exchangeresin ("IRA-120B"/"IRA-402", product of Japan Organo Co., Ltd.). Thethus-desalted aqueous solution was lyophilized to obtain 20 g of apolyether polymer. An NMR analysis revealed that this polymer is apolymer (a molar ratio, p/q between individual structural units p and q:90/10) having the following structural units: ##STR18##

NMR (D₂ O, 200 MHz, ppm): 2.95(6H,s, --N--CH₃), 3.10-3.55(11H,m, --CH₂--CH--O--, --CH₂ --N⁺ --CH₂ --CH₂ --OH), 3.55-4.00(4H,m, --N⁺ --CH₂--CH₂ --OH, --N⁺ --CH₂ --COO⁻).

Molecular weight (GPC, 0.5 wt. % aqueous solution, 50 mM LiBr, PEGstandard): Mw=663,000; Mn=30,000.

Preparation Example 9

An autoclave purged with nitrogen was charged with 15 g ofpolyepichlorohydrin ("Gechron® 1000", product of Nippon Zeon Co., Ltd.),6.1 g of sodium sulfite and 100 g of ion-exchanged water. After thesystem was hermetically sealed to conduct a reaction at 150° C. for 10hours, the system was opened to distill off the ion-exchanged water. Thereaction system was purged with nitrogen, and 135 g ofN-methyl-pyrrolidone were added to the residue. Dimethylamine (gas) wasintroduced into the autoclave to dissolve in the reaction solution.After the system was hermetically sealed to conduct a reaction at 120°C. for 10 hours, the system was opened to remove effluent gas. After thereaction solution was cooled to room temperature, and the resultantprecipitate was collected by filtration, the precipitate was subjectedto reprecipitation in isopropyl ether in an amount 10 times of theprecipitate. The resultant precipitate was dissolved in ion-exchangedwater, and the aqueous solution was subjected to a desalting treatmentwith a strongly basic ion-exchange resin ("IRA-402", product of JapanOrgano Co., Ltd.) and then lyophilized, thereby obtaining 10 g of anaminated polymer.

In a reaction vessel equipped with a reflux condenser, 15.35 g of sodiummonochloroacetate were then suspended in 200 g of ethanol. After 10 g ofthe aminated polymer were added to the suspension with stirring,ion-exchanged water was added until the suspended sodiummonochloroacetate was dissolved. After a reaction was conducted for 36hours under reflux, the reaction solution was subjected toreprecipitation in acetone in an amount 10 times of the reactionsolution. The resultant precipitate was dissolved in ion-exchangedwater, and the aqueous solution was then lyophilized to obtain 9 g of apolyether polymer. An NMR analysis revealed that this polymer is apolymer (a molar ratio, p/q between individual structural units p and q:90/10) having the following structural units: ##STR19##

NMR (D₂ O, 200 MHz, ppm): 2.95(2H,brs, --CH₂ --SO₃ Na), 3.27 (6H,s, --N⁺(CH₃)₂), 3.5-4.34(7H,m, --CH₂ --CH--O, --CH₂ --N⁺ --CH₂ --COO⁻).

Molecular weight (GPC, 0.5 wt. % aqueous solution, 50 mM LiBr, PEGstandard): Mw=3,000; Mn=2,200.

Preparation Example 10

In an autoclave purged with nitrogen, 15 g of polyepichlorohydrin("Gechron® 1000", product of Nippon Zeon Co., Ltd.) were dissolved in200 g of N-methylpyrrolidone while stirring at 50° C. The solution wasthen chilled with ice water. A 50% aqueous solution of dimethylamine inan amount of 146 g was heated to 80° C., and dimethylamine gas generatedwas introduced into the autoclave to dissolve in the reaction solutionwhile bubbling until the dimethylamine gas ceased to be generated. Afterthe system was hermetically sealed to conduct a reaction at 120° C. for12 hours, the system was opened to remove effluent gas. The reactionsolution was cooled to room temperature and then subjected toreprecipitation in isopropyl ether in an amount 10 times of the reactionsolution. The resultant precipitate was dissolved in ion-exchangedwater, and the aqueous solution was subjected to a desalting treatmentwith a strongly basic ion-exchange resin ("IRA-402", product of JapanOrgano Co., Ltd.) and then lyophilized, thereby obtaining an aminatedpolymer.

In a reaction vessel purged with nitrogen, 13.51 g of the aminatedpolymer were dissolved in 150 g of absolute ethanol to keep thetemperature of the solution at 35° C. To the solution, 7.4 g ofβ-propiolactone were added, thereby conducting a reaction at 35° C. for6 hours. The resultant precipitate was collected by filtration,dissolved in water and then subjected to reprecipitation in a mixedsolvent of ethanol/acetone (1/2 v/v) in an amount 10 times of theaqueous solution. The resultant precipitate was dissolved inion-exchanged water, and the aqueous solution was treated with acation/anion mixed type ion-exchange resin ("IRA-120B"/"IRA-402",product of Japan Organo Co., Ltd.) and lyophilized, thereby obtaining14.60 g of a polyether polymer. An NMR analysis revealed that thispolymer is a polyoxyethylene-dimethylaminocarbobetaine polymer havingthe following structural units: ##STR20##

NMR (D₂ O, 200 MHz, ppm): 3.7(6H, s, --N(CH₃)₂), 3.5-4.34(9H,m, --CH₂--CH--O--, --CH₂ --N⁺ --(CH₂)₂ --COO⁻).

Molecular weight (GPC, 0.2M phosphate buffer, PEG standard): Mw=20,000;Mn=15,000.

Test Example 1

With respect to individual ingredients shown in Table 1, the moistureretention and the feeling upon use were evaluated. The results are shownin Table 1.

(Evaluation Methods)

Moisture retention

A 0.5% aqueous solution of each sample is prepared, applied to a humanantecubital site air-conditioned at 20° C. and 40% humidity in aproportion of 10 μl per cm² and left to stand for 10 minutes. Before andafter this treatment, the epidermal conductance of the applied site ismeasured by means of a "SKICON-200" (manufactured by IBS Company) todetermine the moisturizing ability of the sample. The moisturizingability is expressed in terms of a ratio of the conductance after thetreatment to the conductance before the treatment.

The above procedure is repeated 10 times, and their average value isregarded as a measurement result.

Besides, the treated site is rinsed with running water and dried with atowel. Upon elapsed time of 10 minutes after the drying, its epidermalconductance is measured in the same manner as described above, therebydetermining the moisturizing ability after the rinsing. The moisturizingability after the rinsing is expressed in terms of a ratio of theconductance after the rinsing to the conductance before the treatment.Feeling upon use:

A 5% aqueous solution of potassium myristate containing 0.2% of eachsample is prepared. After 2 ml of the solution are dropped on the palmof a hand to cause it to thoroughly lather, the hands are rinsed withrunning water and dried with a towel. After about 5 minutes, the feelinggiven to the palms is evaluated in accordance with the followingstandard:

Moisturized feeling:

∘: Giving a moisturized feeling;

Δ: Somewhat giving a moisturized feeling;

x: Giving no moisturized feeling.

Stickiness to the touch:

∘: Not sticky to the touch;

Δ: Not very sticky to the touch;

x: Sticky to the touch.

                  TABLE 1                                                         ______________________________________                                                          Moistur-                                                                      izing                                                                 Moistur-                                                                              ability  Feel upon use                                                izing   after    Moisturized                                                                             Sticky                                             ability rinsing  feeling   feel                                     ______________________________________                                        Invention product:                                                            1    Compound of                                                                              1.6       1.6    o       o                                         Preparation                                                                   Example 2                                                                2    Compound of                                                                              1.5       1.5    o       o                                         Preparation                                                                   Example 3                                                                3    Compound of                                                                              1.6       1.6    o       o                                         Preparation                                                                   Example 5                                                                4    Compound of                                                                              1.5       1.5    o       o                                         Preparation                                                                   Example 7                                                                Comparative product:                                                          1    Blank      1.0       1.0    x       o                                         (water)                                                                  2    Glycerol   1.7       1.2    .increment.                                                                           .increment.                          3    Cationized 1.3       1.3    .increment.                                                                           x                                         cellulose                                                                ______________________________________                                    

As apparent from the results shown in Table 1, it is understood that allthe invention products have excellent moisturizing ability, which iskept up even after the rinsing, give users a pleasant moisturizedfeeling and are not sticky to the touch.

Formulation Example 1

(Pasty face cleanser)

A pasty face cleanser having the following composition was prepared inaccordance with a method known per se in the art.

The resulting face cleanser gave a refreshed feeling after washing andkept up the moisturized feeling.

    ______________________________________                                        (Composition)           (%)                                                   ______________________________________                                        Sodium sesquilauryl phosphate                                                                         25                                                    Dipotassium myristyl sulfosucinate                                                                    5                                                     Cocoyldiethanolamide    2                                                     Polyethylene glycol monostearate                                                                      4                                                     Hydroxyethylmethylbetaine-polyeter polymer                                                            0.5                                                   (compound of Preparation Example 2)                                           Carboxyvinyl polymer    0.5                                                   Paraben                 0.2                                                   Perfume base            0.3                                                   Purified water          Balance.                                              ______________________________________                                    

Formulation Example 2

(Body shampoo)

A body shampoo having the following composition was prepared inaccordance with a method known per se in the art.

The resulting body shampoo gave no dry skin even after washing and keptup the moisturized feel.

    ______________________________________                                        (Composition)          (%)                                                    ______________________________________                                        Triethanolamine sesquilauryl phosphate                                                               25                                                     Decyl polyglucoside    5                                                      Sodium lauroylsarcosinate                                                                            5                                                      Propylene glycol       5                                                      Dimethylbetaine-polyoxyethylene-diglyceryl                                                           0.5                                                    ether-polyether copolymer (compound of                                        Preparation Example 7)                                                        Octaglyceryl monooleate                                                                              0.2                                                    Perfume base           0.3                                                    Purified water         Balance.                                               ______________________________________                                    

Formulation Example 3

(Shampoo)

A shampoo having the following composition was prepared in accordancewith a method known per se in the art.

The resulting shampoo gave no creaky feeling upon shampooing andrinsing, was not sticky to the touch and gave a moisturized feelingafter shampooing, and kept up the moisturized feeling.

    ______________________________________                                        (Composition)           (%)                                                   ______________________________________                                        Lauryldimethylamine acetate betaine                                                                   10                                                    Sodium N-lauroyl glutamate                                                                            10                                                    Ethylene glycol distearate                                                                            2                                                     Ethylcarbitol           2                                                     Hydroxyethylmethylbetaine-polyeter polymer                                                            1                                                     (compound of Preparation Example 2)                                           Perfume base            0.5                                                   Purified water          Balance.                                              ______________________________________                                    

Formulation Example 4

(Hair treatment)

A hair treatment having the following composition was prepared inaccordance with a method known per se in the art.

The resulting hair treatment was excellent in a softness-impartingeffect on the hair and not sticky to the touch, gave a moisturizedfeeling, and kept up the feeling.

    ______________________________________                                        (Composition)           (%)                                                   ______________________________________                                        Stearyl alcohol         5                                                     Polypeptide (hydrolyzate of collagen)                                                                 5                                                     Stearyltrimethylammonium chloride                                                                     3                                                     Liquid paraffin         3                                                     Hydroxyethylmethylbetaine-polyeter polymer                                                            2                                                     (compound of Preparation Example 2)                                           Ethylcarbitol           1                                                     Perfume base            0.5                                                   Purified water          Balance.                                              ______________________________________                                    

Formulation Example 5

(Lotion)

A lotion having the following composition was prepared in accordancewith a method known per se in the art.

The resulting lotion was not sticky to the touch, gave a moisturizedfeeling, had sufficient moisture retention hardly being washed away bysweat and kept up the moisturized feeling.

    ______________________________________                                        (Composition)           (%)                                                   ______________________________________                                        Ethanol                 10                                                    Glycerol                5                                                     Polyoxyethylene (20) oleyl ether                                                                      1                                                     Sodium lactate          0.6                                                   Lactic acid             0.2                                                   Hydroxyethylmethylbetaine-polyeter polymer                                                            0.2                                                   (compound of Preparation Example 2)                                           Perfume base            0.3                                                   Purified water          Balance.                                              ______________________________________                                    

Formulation Example 6

(Bath additive composition)

A bath additive composition having the following composition was wasprepared in accordance with a method known Per se in the art.

The resulting bath additive composition was excellent in a moisturizingeffect on the skin, gave a moisturized feeling and kept up the feeling.

    ______________________________________                                        (Composition)           (%)                                                   ______________________________________                                        Sodium hydrogencarbonate                                                                              66                                                    Dextrin                 30                                                    Hydroxyethylmethylbetaine-polyeter polymer                                                            3                                                     (compound of Preparation Example 2)                                           Perfume base            0.5                                                   Coloring matter         0.5.                                                  ______________________________________                                    

INDUSTRIAL APPLICABILITY

The polyether polymers according to the present invention are excellentin moisture retention (water retention), adsorptivity andhydrophilicity, and cosmetic and detergent compositions containing thesepolymers keep up an excellent moisturizing effect over a long period oftime and give a pleasant feeling.

We claim:
 1. A polyether polymer having structural units represented bythe following general formula (1): ##STR21## wherein R1 and R2 meanindividually an alkyl group of 1-20 carbon atoms, which may have one ormore hydroxyl groups, and Y denotes an alkylene group of 1-10 carbonatoms, which may have a hydroxyl group; said polyether polymer having aweight-average molecular weight of 5,000-1,000,000.
 2. The polyetherpolymer according to claim 1, wherein said structural unit isrepresented by the following formula (a), (b), (c) or ( d): ##STR22##wherein A and D mean, independently of each other, a hydrogen atom or ahydroxyl group, u and v are, independently of each other, a number of1-20, and w is a number of 1-10.
 3. The polyether polymer according toclaim 1, wherein said structural unit represented by the general formula(1) is represented by the following formula (a-1), (a-2), (a-3) or(d-1): ##STR23##
 4. The polyether polymer according to claim 1, whichfurther has one or more kinds of structural units selected from thoserepresented by the following formulae (e) to (i): ##STR24## wherein inthe formula (e), R³ means --H, --CH₃, --CH₂ OH, --CH₂ --O--CH₂CH(OH)--CH₂ OH, --CH₂ OR⁸, --CH₂ SR⁸ or --CH₂ S(CH₂)₃ SR⁸ in which R⁸ isan alkyl, alkenyl, cycloalkyl, aralkyl or aryl group having 1-20 carbonatoms; in the formula (g), R⁴ denotes a cationic group represented bythe following formula (g-1), (g-2) or (g-3): ##STR25## wherein b and care individually a number of 1-10, is a number of 0-2, e is a number of0-3, f is a number of 1-20, and X⁻ denotes a counter anion; in theformula (h), R⁵ means --SO₃ M or --O--CH₂ --COOM in which M is a metalion or a hydrogen atom; and in the formula (i), R⁶ and R₇ meanindividually an alkyl group of 1-20 carbon atoms, which may have one ormore hydroxyl groups, and a is a number of 1-10.
 5. A process forpreparing a polyether polymer having structural units represented by thegeneral formula (1): ##STR26## wherein R1 and R2 mean individually analkyl group of 1-20 carbon atoms, which may have one or more hydroxylgroups, and Y denotes an alkylene group of 1-10 carbon atoms, which mayhave a hydroxyl group, said polyether polymer having a weight-averagemolecular weight of 5,000-1,000,000, which process comprises reacting apolymer having structural units represented by the general formula (2):##STR27## wherein R¹ and R² have the same meaning as defined above, witha ω-halocarboxylic acid or a salt thereof represented by the followinggeneral formula (3) or a cyclic lactone represented by the followinggeneral formula (4): ##STR28## wherein Y has the same meaning as definedabove, Z denotes a halogen atom, M is a metal ion or a hydrogen atom,and m stands for a number of 1-8.
 6. A moisturizer comprising, as anactive ingredient, the polyether polymer according to claim
 1. 7. Acosmetic composition comprising the polyether polymer according toclaim
 1. 8. A detergent composition comprising the polyether polymeraccording to claim 1 and detergent ingredients.
 9. A detergentcomposition comprising the polyether polymer according to claim 1 anddetergent ingredients.
 10. A detergent composition comprising thepolyether polymer according to claim 1 and detergent ingredients.